NFL Trade Deadline: 30 greatest trades in NFL history

30. Chargers trade up for Ryan Leaf

Back in 1998, there were plenty of teams in need of help at the quarterback position. Two of those teams were the Indianapolis Colts and the then-San Diego Chargers.

While the Colts were fortunate to have the top overall pick that year, landing one of the greatest quarterbacks the NFL has ever seen in Peyton Manning, the Chargers decided to trade up one spot with the Arizona Cardinals to select Ryan Leaf. Unfortunately, Leaf didn’t even come close to having a stellar career.

Heading into the draft, Manning and Leaf were viewed as the top quarterbacks from their class. This shouldn’t seem surprising when looking at the numbers they put together during their college careers.

But in order for San Diego to make sure they landed one of these quarterbacks, since Indianapolis seemed undecided about which player the Colts would take at No. 1, the Chargers swapped first-round picks with Arizona, along with a few others, including a future first-round pick.

By taking this approach, the Chargers would be guaranteed to land at least Manning or Leaf, depending on what the Colts did at No. 1. As every football fan knows, this will always be considered one of the biggest “what if” scenarios the NFL has ever seen. One can only imagine if Indianapolis decided to go the other way and drafted Leaf over Manning.

It only took three years for San Diego to eventually release Leaf. The former Washington State Cougars star will always be considered one of the biggest draft busts of all-time, especially since he missed the entire 1999 season due to a shoulder injury.

Little did the Chargers know that six years later they would be dealing with even more quarterback drama from the draft, but more on that in a little bit.